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The Fork-and-Edit Sin: Why I Took on Deliberate Tech Debt (And Paid It Off with Tokens)
Every seasoned software engineer has an internal alarm that rings the second they duplicate code. We’ve had the rules beaten into us for decades: Don’t Repeat Yourself (DRY). Abstract early. Build configurable components. How about- never fork a whole repo just to swap out data 😂 Last week, I ignored every single one of those…
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When the Web Was Actively Trying to Kill You: A Field Guide to Early Front-End Lore
In the ongoing retrospective series I have kicked off on LinkedIn and YouTube about the maturation of the web platform, I am going to be focusing on how Boston and Cambridge served as ground zero for modern front-end engineering between 2008 and 2013. We will talk about the launch of HTML5 Boilerplate, the transition to…
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TypeScript Won. Now It’s Giving Up Its Superpowers.
When you spin up a greenfield project on a Tuesday afternoon, a build step feels like a completely reasonable trade-off. You install a bundler, configure a transpiler, sprinkle in a few TypeScript-specific conveniences, and marvel at the developer ergonomics. Having the compiler quietly invent runtime JavaScript out of thin air to support an enum, a…
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The Superset Trap: Why Node’s Native TypeScript is Going to Break Enterprise Brains
If you spend your time in open-source mailing lists or arguing about AST transformations on social media, the recent push toward “erasable syntax” makes total sense. I’ve been a proponent of TypeScript for a long time. In the early days, whenever someone brought up enum, for example, I remember having conversations along the lines of:…
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Governing the Generative Drift: Why We Need the Assumptions & Constraints Manifest (ACM)
A couple of weeks ago, I talked about the “Happy Path Trap”—how LLMs create massive Day 1 velocity while burying teams in silent Day 2 architectural debt. During that discussion, I pitched an idea: What if we required an Assumptions & Constraints Manifest (ACM) in every AI-assisted PR to make hidden trade-offs visible? Since I’m…